Tandem electrophilic/nucleophilic additions to tungsten-coordinated furans

ORGN 381

Kimberley C Bassett, kcb6j@virginia.edu1, Matthew Olsen, mo2c@virginia.edu1, William H. Myers2, Michal Sabat, ms5c@virginia.edu1, and W. Dean Harman1. (1) Department of Chemistry, University of Virginia, McCormick Rd, P.O. Box 400-319, Charlottesville, VA 22904, (2) Department of Chemistry, University of Richmond
{TpW(NO)PMe3}, where Tp = hydridotris(pyrazolyl)borate, is capable of coordinating to furans in an η2- fashion. This coordination activates the β-carbon of the furan, making it more nucleophillic. The π-basic metal fragment stabilizes both the furanium and/or ring-opened intermediates, that are formed as a result of the reactions with aldehydes, α,β- unsaturated ketones, and other electorphiles. The furanium is then quenched with a suitable nucleophile to give substituted dihydrofurans and cyclopentene cores in respectable yields.

 

Bioorganic, Metal-Mediated Reactions, and Molecular Recognition
8:00 PM-10:00 PM, Tuesday, 30 August 2005 Washington DC Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005